I could never get into wipeout, and I just tried again, something about the controls just doesn't gel for me! N-Gen racing on the other hand, that was my crack!
I loved the savage fast 60fps one on the ps3, that was intense, it's all about the air brakes! Rollcage was more my thing though, loved Grip the modern homage remake of it check that out if you haven't!
2097 and Wip3out improved the controls and track clipping mechanics dramatically, Wipeout 1 is kind of janky. However playing it in a browser = pure nostalgia for one of my first PC games.
For me, Wipeout Fusion on the PS2 was the pinnacle of the game series, though admittedly I haven't really played much of anything beyond that, excepting the PSP versions which were also awesome.